U.S. patent number 6,090,774 [Application Number 09/169,994] was granted by the patent office on 2000-07-18 for single phase liquid mixture of benzophenone and mixture of at least two other normally solid perfumery substances and perfumery uses thereof.
This patent grant is currently assigned to International Flavors & Fragrances Inc.. Invention is credited to Murray Moscona, Mark A. Sprecker, Richard A. Weiss.
United States Patent |
6,090,774 |
Moscona , et al. |
July 18, 2000 |
Single phase liquid mixture of benzophenone and mixture of at least
two other normally solid perfumery substances and perfumery uses
thereof
Abstract
Described is a single phase liquid mixture of benzophenone and a
mixture of at least two other normally solid perfumery substances
which mixture contains from about 25% up to about 60% by weight of
benzophenone and from about 60% down to about 25% by weight of a
mixture of normally crystalline perfumery ingredients, each of
which has a melting point of between about 35.degree. C. and about
120.degree. C. at about 1 atmosphere pressure, containing at least
two substances of the following classes: (i) coumarin derivatives;
(ii) vanillin derivatives; (iii) resorcylic acid derivatives; (iv)
methylene dioxybenzene derivatives; (v)
trichloro-.alpha.-phenylethyl esters; (vi) polycyclic musks; (vii)
aryl alkanoic acids; and (viii) p-oxoalkylphenols and uses of such
mixtures in augmenting or enhancing the aroma of perfume
compositions, colognes and perfumed articles, including but not
limited to solid or liquid anionic, cationic, nonionic or
zwitterionic detergents, fabric softener compositions, fabric
softener articles, hair preparations, cosmetic powders and perfumed
polymers.
Inventors: |
Moscona; Murray (Rumson,
NJ), Sprecker; Mark A. (Sea Bright, NJ), Weiss; Richard
A. (Livingston, NJ) |
Assignee: |
International Flavors &
Fragrances Inc. (New York, NY)
|
Family
ID: |
22618078 |
Appl.
No.: |
09/169,994 |
Filed: |
October 13, 1998 |
Current U.S.
Class: |
512/20; 510/101;
524/1; 512/26; 512/21; 512/25 |
Current CPC
Class: |
C11B
9/00 (20130101); A61L 9/01 (20130101); A61Q
13/00 (20130101); C11D 3/50 (20130101); A61K
8/02 (20130101); A61K 8/35 (20130101) |
Current International
Class: |
C11D
3/50 (20060101); C11B 9/00 (20060101); A61K
007/46 (); C11D 003/50 (); C11D 009/44 (); C08J
003/40 (); C08L 003/40 () |
Field of
Search: |
;512/20,21,25,26
;510/101 ;524/1 |
References Cited
[Referenced By]
U.S. Patent Documents
Foreign Patent Documents
Primary Examiner: Harris; Cynthia
Assistant Examiner: Cole; Monique T.
Claims
What is claimed is:
1. A single phase liquid eutectic mixture which is in the liquid
phase at a temperature T.sub.L above, at most, about 20.degree. C.
and at about 1 atmosphere absolute pressure, satisfying the
conditions:
wherein T.sub.max. is the temperature of the point of liquid-solid
phase change, containing the following ingredients in the following
percentage ranges:
(a) coumarin having the structure: ##STR34## (b) ethyl vanillin
having the structure: ##STR35## (c) heliotropin having the
structure: ##STR36## (d) the compound having the structure:
##STR37## (e) benzophenone having the structure: ##STR38## (f)
benzoic acid having the structure: ##STR39## (g) the compound
having the structure: ##STR40## (h) a mixture of compounds having
the structures: ##STR41## (i) a mixture of compounds having the
structures: ##STR42## (j) the compound having the structure:
##STR43## (k) the compound having the structure: ##STR44##
2. The composition of claim 1 containing the ingredients:
3. The composition of claim 1 containing the following
ingredients:
4. The composition of claim 1 containing the following
ingredients:
5. The composition of claim 1 containing the following
ingredients:
6. A process for augmenting or enhancing the aroma of a perfume
composition comprising the step of adding to said perfume
composition an aroma augmenting or enhancing quantity of the
composition of matter defined according to claim 1.
7. A process for augmenting or enhancing the aroma of a liquid
anionic, nonionic, cationic or zwitterionic detergent comprising
the step of intimately admixing with said liquid anionic, nonionic,
cationic or zwitterionic detergent an aroma augmenting or enhancing
quantity of the composition of matter defined according to claim
1.
8. A process for augmenting or enhancing the aroma of a
thermoplastic polymer comprising the step of intimately admixing
with said thermoplastic polymer in the liquid state an aroma
augmenting or enhancing quantity of the composition of matter
defined according to claim 1.
Description
BACKGROUND OF THE INVENTION
This invention relates to a single phase liquid mixture of
benzophenone and mixture of at least two other normally solid
perfumery substances. Furthermore, this invention relates to a
novel method of preparing homogeneous benzophenone-containing
liquid mixtures of solid perfume materials and the use of these
mixtures for preparing solvent-free, ready made perfume
formulations.
As stated in U.S. Pat. No. 5,518,997 issued on May 21, 1996, the
specification for which is incorporated by reference herein, for
application reasons (e.g., stability, odor intensity or
substantivity), solid perfumery materials are being increasingly
used in the modern perfume industry. These substances are
indispensible in particular for perfumes for detergents and
softeners, since these products are subjected to considerable
stresses during preparation, in the market and subsequently during
processing. The fragrance of these products is not only of decisive
importance in decisions for or against the purchase of a certain
product, but also accompanies the product from production through
storage to use. In addition, the laundry which has been washed or
treated with a softener must have a pleasant odor, even after weeks
of storage, in order to meet the high quality expectations of the
buyer of a branded article.
Furthermore, as stated in U.S. Pat. No. 5,518,997, for mixing
perfume materials, the chemically stable, liquid components are
usually initially introduced, as a rule with the addition of
further solvents, such as dipropylene glycol or diethyl phthalate,
and the solid components are added gradually with vigorous
stirring, the mixture being heated externally or by means of
internal heating coils until the solids melt or go into solution.
Since the heating surfaces are required to be heated to relatively
high temperatures in order to achieve sufficient heat transport, a
certain amount of damage occurs at these heating surfaces as a
result of overheating, particularly in the case of sensitive
substances. Moreover, the vigorous mixing results in greater
contact with air, so that it is necessary to work under an
expensive inert gas atmosphere in order to avoid damage by
oxidation.
Furthermore, as stated in U.S. Pat. No. 5,518,997, after
dissolution of the solids, the mixture is cooled. Sensitive,
readily volatile or chemically unstable materials are then added
with gentle stirring, and stirring is continued until the mixture
is homogeneous. This method is considerably time-consuming, since a
disadvantageous solid/liquid mixing ratio is initially present, or
a time-consuming heating and cooling process is necessary in
between, and the use of additional solvents not only incurs costs
and unnecessarily increases the processing quantities, but also
additionally pollutes the environment.
U.S. Pat. No. 5,518,997 discloses a method of preparing stable
liquid perfume material mixtures with a high solid content. More
specifically, U.S. Pat. No. 5,518,997 discloses a method of
preparing homogeneous mixtures of liquid and/or solid perfume
materials by mixing the components and liquefying the mixture in
which a binary or ternary eutectic premix which is liquid at room
temperature and contains 10-90% of the individual substances in the
case of binary mixtures and 10-70% in the case of ternary mixtures
is formed from:
(a) the solid
6-acetyl-1,1,3,4,4,6-hexamethyltetra-hydronaphthalene;
(b) the solid or oily .alpha.,n-hexylcinnamaldehyde (having the
structure: ##STR1## (c) the oily
p-tert-butyl-.alpha.,n-methhylhydroinnamaldehyde (having the
structure: ##STR2## (d) the solid p-methoxyacetophenone (having the
structure: ##STR3## (e) the solid benzyl o-hydroxybenzoate (having
the structure: ##STR4## and the remaining solid and liquid products
are introduced into this mixture simultaneously or in a sequence
which is freely chosen for the particular mixture and is
independent of the chemical and physical nature of the substances,
and the binary and ternary eutectic premixes prepared in this
manner.
In addition, U.S. Pat. No. 4,650,603 issued on Mar. 17, 1987 (the
specification for which is incorporated by reference herein)
discloses a single phase liquid mixture of tricyclic isochroman
derivative mixture and acetyl tetrahydronaphthalene derivative
mixture. More specifically, U.S. Pat. No. 4,650,603 discloses a
liquid mixture of tricyclic isochroman derivatives having as a
major component the compound having the structure: ##STR5## and
acetyl tetrahydronaphthalene derivatives having as a major
component the compound having the structure: ##STR6## and uses of
such mixtures in augmenting or enhancing the aroma of perfume
compositions, colognes and perfumed articles.
Neither of the aforementioned U.S. Pat. No. 4,650,603 or U.S. Pat.
No. 5,518,997, discloses or infers the unexpectedly great
versatility of the use of benzophenone in forming single phase
liquid perfumery mixtures from ordinarily solid and crystalline
individual components. It is particularly noteworthy that on mixing
of the components with the benzophenone, the mixing occurs with an
overall cooling effect (endothermic mixing) which is advantageous
in utilizing heat-unstable materials.
THE INVENTION
Our invention is directed to a single phase liquid eutectic mixture
which is in the liquid phase at a temperature T.sub.L above, at
most, about 20.degree. C. at about 1 atmosphere absolute pressure,
satisfying the conditions:
where T.sub.max. is the temperature at the point of liquid-solid
phase change, containing:
(a) from about 25% by weight up to about 60% by weight of
benzophenone having the structure: ##STR7## (b) from about 60% down
to about 25% by weight of a mixture of crystalline ingredients,
each of which has a melting point defined by the inequality:
containing at least two substances selected from the following
classes of substances:
(i) a coumarin derivative defined according to the structure:
##STR8## wherein R.sub.1, R.sub.2, R.sub.3 and R.sub.4 represent
hydrogen, or one of R.sub.1, R.sub.2, R.sub.3 and R.sub.4 is
C.sub.1 -C.sub.3 alkyl or C.sub.1 -C.sub.3 alkoxy, and the other of
R.sub.1, R.sub.2, R.sub.3 and R.sub.4 is hydrogen; and wherein
R.sub.5 and R.sub.5 ' represents hydrogen or one of R.sub.5 and
R.sub.5 ' is C.sub.1 -C.sub.3 alkyl and the other of
R.sub.5 and R.sub.5 ' is hydrogen;
(ii) a vanillin derivative defined according to the structure:
##STR9## wherein R.sub.6 is C.sub.1 -C.sub.3 alkyl and R.sub.7 is
hydrogen or C.sub.1 -C.sub.3 alkyl;
(iii) a resorcylic acid derivative defined according to the
structure: ##STR10## wherein R.sub.8, R.sub.9 and R.sub.10 are the
same or different C.sub.1 -C.sub.3 alkyl;
(iv) a methylene dioxybenzene derivative having the structure:
##STR11## wherein R.sub.11 is carboxaldehyde or C.sub.3 -C.sub.5
oxoalkyl; (v) a trichloro-.alpha.-phenylethyl ester having the
structure: ##STR12## wherein R.sub.12 is C.sub.1 -C.sub.3 alkyl;
(vi) a polycyclic musk defined according to the structure:
##STR13## wherein Z is, in the alternative, one of the moieties:
##STR14## and wherein one of R.sub.13, R.sub.14, R.sub.15 and
R.sub.16 is acetyl and the other of R.sub.13, R.sub.14, R.sub.15
and R.sub.16 are hydrogen or C.sub.1 -C.sub.4 lower alkyl or
R.sub.14 and R.sub.15 complete an alkyl substituted or
unsubstituted alkylenyloxyalkylene moiety containing from 3 up to 6
carbon atoms and R.sub.13 and R.sub.16 are hydrogen or methyl;
wherein R.sub.17, R.sub.18, R.sub.19, R.sub.20, R.sub.21, R.sub.22,
R.sub.18 ' and R.sub.21 ' are the same or different hydrogen,
methyl or ethyl;
(vii) an aryl alkanoic acid defined according to the structure:
##STR15## wherein N is 0 or 1 and Q is C.sub.2 -C.sub.4 alkenylene
when N is 1; (viii) a .beta.-naphthyl ether defined according to
the structure: ##STR16## wherein R.sub.24 is C.sub.1 -C.sub.3
alkyl; and (ix) a p-oxoalkylphenol defined according to the
structure: ##STR17## Our invention is also directed to the use of
such mixtures in augmenting, enhancing or imparting an aroma in or
to perfume compositions, colognes and perfumed articles, including
but not limited to solid or liquid anionic, cationic, nonionic or
zwitterionic detergents, fabric softener compositions, fabric
softener articles, hair preparations, cosmetic powders and perfumed
polymers.
The preferred coumarin derivatives are coumarin having the
structure: ##STR18## having a melting point of 68.degree. C.;
5-ethyl coumarin having the structure: ##STR19## having a melting
point of 70.degree. C.; and MARANIOL.RTM. (trademark of
Givaudan-Roure S.A. of Basel, Switzerland) having the structure:
##STR20## with a melting point of 114.degree. C.
Preferred vanillin derivatives useful in the practice of our
invention are: ethyl vanillin having the structure: ##STR21##
having a melting point of 65.degree. C. and vanillin having the
structure: ##STR22## having a melting point of 83.degree. C. The
preferred resorcylic acid derivative is VERAMOSS.RTM. (trademark of
International Flavors & Fragrances Inc. of New York, N.Y.,
U.S.A.) having the structure: ##STR23##
A preferred methylene dioxybenzene derivative is heliotropin having
the structure: ##STR24## and having a melting point of 37.degree.
C.
A preferred trichloro-.alpha.-phenylethyl ester is ROSETONE.TM.
(trademark of International Flavors & Fragrances Inc.) having
the structure: ##STR25## and a melting point of 88.degree. C.
Preferred polycyclic musks useful in the practice of our invention
are as follows:
(a) CELESTOLIDE.RTM. (registered trademark of International Flavors
& Fragrances Inc.) having the structure: ##STR26## and a
melting point of 76.degree. C.; (b) TONALID.RTM. (registered
trademark of Hercules, Inc. of Wilmington, Del.), a mixture of
compounds having the structures: ##STR27## (c) GALAXOLIDE.RTM.
(registered trademark of International Flavors & Fragrances
Inc.), a mixture of compounds having the structures: ##STR28##
Preferred aryl alkanoic acids useful in the practice of our
invention are:
(a) benzoic acid having the structure: ##STR29## (b) cinnamic acid
having the structure: ##STR30##
The preferred .beta.-naphthoether useful in the practice of our
invention is "yara yara" having the structure: ##STR31## and a
melting point of 73.degree. C.
The p-oxoalkylphenol used in the practice of our invention is
OXYPHENYLON.TM. (trademark of International Flavors &
Fragrances Inc.) having the structure: ##STR32## and a melting
point of 82.degree. C.
An additional methylenedioxybenzene derivative preferred in the
practice of our invention is DULCINYL.TM. (trademark of
International Flavors & Fragrances Inc.) having the structure:
##STR33## and a melting point of 43.degree. C.
Preferred mixtures including their ranges of weight percents useful
in the practice of our invention are as follows:
______________________________________ Range of Weight Ingredient
Percentages ______________________________________ Coumarin 6-30%
Ethyl vanillin 8-15% Heliotropin 7-15% VERAMOSS .RTM. 0-40%
Benzophenone 25-60% Benzoic acid 0-12% CELESTOLIDE .RTM. 0-40%
TONALID .RTM. 0-40% GALAXOLIDE .RTM. 0-40% OXYPHENYLON .TM. 0-2%
DULCINYL .TM. 0-2% ______________________________________
It is important to note that on preparing the aforementioned
mixtures, a cooling effect occurs, that is the energy of mixing
causes a reduction in the temperature of the mixture. This
temperature reduction is advantageous in that certain
temperature-sensitive materials are not exposed to excessive heat.
Furthermore, the entire mixture is not exposed to excessive heat
which occurs in other procedures in preparing perfumes. This
cooling effect is unexpected and advantageous in preparing the
mixtures of our invention.
The liquid mixture containing benzophenone of our invention and one
or more auxiliary perfume ingredients including alcohols,
aldehydes, nitriles, esters, cyclic esters, ketones, ethers,
natural essential oils and synthetic essential oils may be admixed
so that the combined odors of the individual components produce a
pleasant and desired fragrance. Such perfume compositions usually
contain:
(a) the main note or the "bouquet" or foundation stone of the
composition;
(b) modifiers which round off and accompany the main note;
(c) fixatives which include odorous substances which lend a
particular note to the perfume throughout all stages of evaporation
and substances which retard evaporation; and
(d) topnotes which are usually low-boiling, fresh smelling
materials.
In perfume compositions, it is the individual components which
contribute to its particular olfactory characteristics, but the
overall effect of the perfume composition will be the sum of the
effects of each of the ingredients. Thus, the liquid
benzophenone-containing mixture of our invention and one or more
auxiliary perfume ingredients can be used to alter the aroma
characteristics of a perfume composition, for example, by utilizing
or moderating the olfactory reaction contributed by a least one
other ingredient in the composition.
The amount of liquid benzophenone-containing mixture of our
invention and one or more auxiliary perfume ingredients of our
invention can range up to 100% of the fragrance components employed
in a perfume article and can range up to 10% of the weight of the
perfumed article and will depend upon considerations of cost,
nature of the end product, the effect desired on the finished
product and the particular fragrance sought.
The liquid benzophenone-containing mixture of our invention and one
or more perfume ingredients are useful, taken alone or in perfume
compositions as olfactory components in anionic, cationic and
nonionic detergents, soaps, fabric softener compositions, fabric
softener articles for use in clothes dryers (e.g., BOUNCE.RTM., a
registered trademark of the Procter & Gamble Company of
Cincinnati, Ohio), space odorants and deodorants, perfumes,
colognes, toilet water, bath preparations, such as lacquers,
brilliantines, creams, deodorants, hand lotions and sun screens;
powders such as talcs, dusting powders, face powders and the like.
When used as an olfactory component in perfume compositions or in a
perfumed article such as anionic, nonionic, cationic and
zwitterionic detergents and in fabric softener compositions and
fabric softener articles, as little as 0.05% of the liquid
benzophenone mixture of our invention and one or more auxiliary
perfume ingredients will suffice to impart a fragrance, such as a
musk fragrance. Generally no more than 10% of the liquid
benzophenone-containing mixture of our invention and one or more
auxiliary perfume ingredients based on the ultimate end product is
required in a perfumed article.
The benzophenone-containing liquid composition of our invention can
also be used in a carrier and can be encapsulated in such a
carrier. Such a carrier can be an absorbent solid such as a gum
(e.g., gum arabic or xanthan gum) or components for encapsulating
the composition are exemplified by gelatin which is used in
coacervation processes.
It will thus be apparent that the benzophenone-containing liquid
mixture of our invention and one or more auxiliary perfume
ingredients (if desired) can be used to alter the sensory
properties, particularly organoleptic properties of a wide variety
of consumable fragranced materials.
BRIEF DESCRIPTION OF THE DRAWINGS
FIG. 1 is a phase diagram plotting melting point in degrees
Centigrade versus percent of benzophenone in the mixture which also
contains the following substances:
5 parts coumarin;
6 parts ethyl vanillin;
5 parts heliotropin; and
15 parts VERAMOSS.RTM..
FIG. 2 represents a cutaway side elevation view of apparatus used
in forming perfumed polymers, containing a liquid single phase
benzophenone-containing mixture of our invention.
FIG. 3 is a front view of the apparatus of FIG. 2, looking in the
direction of the arrows.
DETAILED DESCRIPTION OF THE DRAWINGS
FIG. 1 is a plot showing melting point and degrees Centigrade
versus percent benzophenone in a mixture which also includes:
5 parts by weight coumarin;
6 parts by weight ethyl vanillin;
5 parts by weight heliotropin; and
15 parts by weight VERAMOSS.RTM.
The percent benzophenone is shown on the X axis, which X axis is
indicated by reference numeral 19. The melting point is shown on
the Y axis, which Y axis is indicated by reference numeral 20. The
graph showing phase separation is indicated by reference numeral
10, with the eutectic point indicated by reference numeral 14.
The data point indicated by reference numeral 11 is for 100%
benzophenone and no other components of the mixture. The data point
indicated by reference numeral 12 is for 85% benzophenone. The data
point indicated by reference numeral 13 is for 70% benzophenone.
The data point (eutectic) indicated by reference numeral 14 is for
51.5% benzophenone, with the resultant mixture having a melting
point of -12.degree. C. The data point indicated by reference
numeral 15 is for 42% benzophenone. The data point indicated by
reference numeral 16 is for 36% benzophenone. The data point
indicated by reference numeral 17 is for 21% benzophenone. The data
point indicated by reference numeral 18 is for a mixture containing
11.4% benzophenone.
Referring to FIGS. 2 and 3, there is provided a process for forming
scented polymer elements (wherein the polymer may be a
thermoplastic polymer such as low density polyethylene or
polypropylene or copolymers of ethylene-vinyl acetate or mixtures
of a polymer and a copolymer such as a copolymer of ethylene-vinyl
acetate and polyethylene), such as pellets useful in the formation
of plastic particles useful in fabricating certain articles which
may be perfumed. The process comprises heating the polymer or
mixture of polymers to the melting point of said polymer or mixture
of polymers, e.g., 250.degree. C. in the case of low density
polyethylene. The lower-most portion of the container is maintained
at a slightly lower temperature, and the material of the container
is taken off at such location for delivery through the conduit.
Thus, referring to FIGS. 2 and 3 in particular, the apparatus used
in producing such elements comprises a device for forming the
polymer containing perfume, e.g., polyethylene or
polyethylene-polyvinyl acetate or mixtures of same or
polypropylene, which comprises a vat or container 212 into which
the polymer taken alone or in admixture with other copolymers and a
perfuming substance containing the benzophenone liquid mixture of
our invention is placed. The container is closed by means of an
airtight lid 228, and the lid is clamped to the container by
airtight bolts 265. A stirrer 273 traverses the lid or cover 228 in
an airtight manner and is rotatable in a suitable manner. A
surrounding cylinder 212A having heating coils which are supplied
with electric current through cable 214 from a rheostat or control
216 is operated to maintain the temperature inside the container
212 such that the polymer in the container will be maintained in
the molten or liquid state. It has been found advantageous to
employ polymers at such a temperature that the viscosity will be in
the range of 90-100 Saybolt seconds. The heater is operated to
maintain the upper portion of the container 212 within a
temperature range of, for example, 250.degree. C. in the case of
low density polyethylene. The bottom portion of the container 212
is heated by means of heating coils 212A, regulated through the
control 220, connected thereto through a connecting wire 222 to
maintain the lower portion of the container 212 within a
temperature range
of 225-240.degree. C.
Thus, the polymer or mixture of polymers added to the container 212
is heated from 10-12 hours, whereafter the perfume composition or
perfume material containing the liquid benzophenone-containing
mixture of our invention is quickly added to the melt. Generally,
about 10-45% by weight of the resulting mixture of the perfumery
substance is added to the polymer.
After the perfume material is added to the container 212, the
mixture is stirred for a few minutes, for example, 5-15 minutes,
and maintained within the temperature ranges indicated previously
by the heating coil 212A. The controls 216 and 220 are connected
through cables 224 and 226 to a suitable supply of electric current
for supplying the power for heating purposes.
Thereafter, the valve V is opened permitting the mass to flow
outwardly through conduit 232 (also indicated by reference numeral
218 in FIG. 2) having a multiplicity of orifices 234 adjacent to
the lower side thereof. The outer end of the conduit 232 is closed
so that the liquid polymer intimately admixed with the perfume
substance containing the benzophenone-containing liquid mixture of
our invention will continuously drop through the orifices 234
downwardly from the conduit 232. During this time, the temperature
of the polymer intimately admixed with the perfumery substance in
the container 212 is accurately controlled so that a temperature in
the range of from about 240-250.degree. C. (in the case of low
density polyethylene) will exist in the conduit 232. The regulation
of the temperature through the control 216 and 220 is essential in
order to insure temperature balance to provide for the continuous
dropping or dripping of molten polymer intimately admixed with the
perfume substance containing the benzophenone-containing liquid
mixture of our invention through the orifices 234 at a rate which
will insure the formation of droplets 236 which will fall
downwardly onto a moving conveyor belt 238 caused to run between
conveyor wheels 240 and 242 beneath the conduit 232.
When the droplets 236 fall onto the conveyor 238, they form pellets
244 which harden almost instantaneously and fall off the end of the
conveyor 238 into a container 245 which is advantageously filled
with water or some other suitable cooling liquid to insure the
rapid cooling of each of the pellets 244. The pellets 244 are then
collected from the container 245 and utilized for formation of
other functional products, e.g., garbage bags and the like. The
belt 238 is continuously cooled by means of the cooling liquid
contained in container 250 having sidewall 248 and containing a
cooling liquid transmission element, e.g., a sponge indicated by
reference numeral 256, with the cooling fluid, e.g., cold water
indicated by reference numeral 254. The sponge 256 transmits the
cooling liquid to the belt 238 to keep the belt cool so that the
polymer containing the benzophenone-containing liquid is solidified
with the benzophenone-containing liquid contained within the
interstices of the polymer.
The following examples are illustrative, and the invention is to be
considered restricted thereto only as indicated in the appended
claims. All parts and percentages given herein are by weight unless
otherwise specified.
EXAMPLE I
PREPARATION OF LIQUID EUTECTIC FRAGRANCE MIXTURES
The following mixtures are prepared, each of which form eutectic
liquid compositions at temperatures indicated in the following
examples. Each of the mixtures, when admixed, gives rise to a
cooling effect resulting from the endothermic energy of mixing:
______________________________________ Weight % of Ingredient in
Composition Ingredients IA IB IC ID IE
______________________________________ Coumarin 10.31 10.31 10.31
10.31 0 Ethyl vanillin 12.37 12.37 12.37 12.37 0 Heliotropin 10.31
10.31 10.31 10.31 0 VERAMOSS .RTM. 20.62 0 10.31 10.31 0 Benzoic
acid 10.31 0 0 0 0 Benzophenone 36.08 36.08 36.08 36.08 33.3
CELESTOLIDE .RTM. 0 30.93 20.62 0 0 TONALID .RTM. 0 0 0 20.62 33.3
GALAXOLIDE .RTM. 0 0 0 0 33.3
______________________________________
The eutectic temperature for Example IA is -15.degree. C. The
eutectic temperature for Example IB is 3.degree. C. The eutectic
temperature for Example IC is -13.degree. C. The eutectic
temperature for Example ID is -17.degree. C. The eutectic
temperature for Example IE is -4.degree. C. The perfume composition
of Example IA has an intense floral, chypre aroma with moss
undertones. The perfume compositions of Example IB, IC and ID have
floral, chypre aromas with moss and musky undertones. The perfume
composition of Example IE has an intense musk aroma with animalic
undertones.
EXAMPLE II
PREPARATION OF LIQUID EUTECTIC FRAGRANCE MIXTURES
The following mixtures are prepared, each of which form eutectic
liquid compositions at temperatures indicated in the following
examples. Each of the mixtures, when admixed, gives rise to a
cooling effect resulting from the endothermic energy of mixing:
______________________________________ Weight % of Ingredient in
Composition Ingredients IIA IIB IIC IID IIE
______________________________________ Coumarin 7.8 18.69 25.64
11.49 9.35 Ethyl vanillin 9.38 11.21 10.26 13.79 11.21 Heliotropin
7.8 9.35 8.55 11.49 9.35 VERAMOSS .RTM. 23.44 28.04 25.64 22.99
37.38 Benzophenone 51.56 32.71 29.91 40.23 32.71
______________________________________
The eutectic point for the composition of Example IIA is
-12.degree. C. The eutectic point for the composition of Example
IIB is 1.degree. C. The eutectic point for the composition of
Example IIC is -11.degree. C. The eutectic point for the
composition of Example IID is -13.degree. C. The eutectic point for
the composition of Example IIE is 21.degree. C.
Each of the perfume compositions of Examples IIA, IIB, IIC, IID and
IIE have floral, chypre aromas with intense moss undertones.
EXAMPLE III
PREPARATION OF A SOAP COMPOSITION
100 Grams of soap chips are admixed with 1 gram of one of the
perfume compositions of Table I below until a substantially
homogeneous composition is obtained. The perfumed soap manifests an
excellent aroma as set forth in Table I below:
TABLE I ______________________________________ Perfume Ingredients
Aroma ______________________________________
Benzophenone-containing liquid mixture Intense floral, of Example
IA chypre aroma with moss undertones. Benzophenone-containing
liquid mixture Floral, chypre aroma of Example IB with moss and
musky undertones. Benzophenone-containing liquid mixture Floral,
chypre aroma of Example IC with moss and musky undertones.
Benzophenone-containing liquid mixture Floral, chypre aroma of
Example ID with moss and musky undertones. Benzophenone-containing
liquid mixture Intense musk aroma of Example IE with animalic
undertones. Benzophenone-containing liquid mixture Floral, chypre
aroma of Example IIA with intense moss undertones.
Benzophenone-containing liquid mixture Floral, chypre aroma of
Example IIB with intense moss undertones. Benzophenone-containing
liquid mixture Floral, chypre aroma of Example IIC with intense
moss undertones. Benzophenone-containing liquid mixture Floral,
chypre aroma of Example IID with intense moss undertones.
Benzophenone-containing liquid mixture Floral, chypre aroma of
Example IIE with intense moss undertones.
______________________________________
EXAMPLE IV
PREPARATION OF A COLOGNE AND HANDKERCHIEF PERFUME
One of the perfume substances as set forth in Table I of Example
III is incorporated into a cologne at concentrations 1.5%, 2.0%,
2.5%, 3.0%, 3.5% and 4.0% in 80%, 85%, 90% and 95% aqueous ethanol;
and into handkerchief perfumes at concentrations of 15%, 20%, 25%
and 30% (in 85%, 90% and 95% aqueous ethanol). Distinct and
definite fragrances as set forth in Table I of Example III are
imparted to the cologne and to the handkerchief perfume at each of
the levels indicated.
EXAMPLE V
PREPARATION OF A COSMETIC POWDER COMPOSITION
A cosmetic powder is prepared by mixing in a ball mill 100 grams of
talcum powder with 0.15 grams of one of the substances of Table I
of Example III. The resulting powders have excellent floral, chypre
aromas.
EXAMPLE VI
Utilizing the procedure of Example I of column 15 of U.S. Pat. No.
3,632,396 (the specification for which is incorporated herein by
reference), a non-woven cloth substrate useful as a dryer-added
fabric softening article of manufacture is prepared wherein the
substrate, the substrate coating, the outer coating and the
perfuming material are as follows:
1. a water "dissolvable" paper ("Dissolvo Paper");
2. Adogen 448 (m.p. about 140.degree. F.) as the substrate coating;
and
3. an outer coating having the following formulation (m.p. about
150.degree. F.):
57% C.sub.20-22 HAPS;
22% isopropyl alcohol;
20% antistatic agent; and
1% of one of the perfume substances of Table I of Example III.
Fabric softening compositions prepared as set forth above, having
an aroma characteristic as set forth in Table I of Example III
essentially consists of a substrate having a weight of about 3
grams per 100 square inches; a substrate coating of about 1.85
grams per 100 square inches of substrate; and an outer coating of
about 1.4 grams per 100 square inches of substrate, thereby
providing a total aromatized substrate and an outer coating weight
ratio of about 1:1 by weight of the substrate. Aromas are imparted
as set forth in Table I of Example III in a pleasant manner to the
head space in the dryer on operation thereof, using the said
dryer-added fabric softening, non-woven fabric.
EXAMPLE VII
PREPARATION OF A SOAP COMPOSITION
100 Grams of soap chips are prepared according to Example V of U.S.
Pat. No. 4,058,490 issued on Nov. 15, 1977, the specification for
which is incorporated by reference herein, as follows:
"The sodium salt of an equal mixture of C.sub.10 -C.sub.14 alkane
sulfonates (95% active), 40 lbs. is dissolved in a mixture of 80
lbs. of anhydrous isopropanol and 125 lbs. of deionized water at
150.degree. F. In this mixture is dissolved 10 lbs. of partially
hydrogenated coconut oil fatty acids and 15 lbs. of sodium
mono-C.sub.14 -alkyl maleate, and the pH of this solution is
adjusted to 5.0 by the addition of a small amount of a 50% aqueous
solution of NaOH. The isopropanol is distilled off and the
remaining aqueous solution is dried. The resulting solid actives
are then blended in a chip mixer with 10 lbs. water, 0.2 lb.
titanium hydroxide."
The resulting blend is then mixed with one of the perfume
substances of Table I of Example III until a substantially
homogeneous composition is obtained. The perfumed soap composition
manifests an aroma as set forth in Table I of Example III.
EXAMPLE VIII
GRANULAR DETERGENT COMPOSITION
A granular detergent composition is prepared according to United
Kingdom Patent No. 1,501,498, the specification for which is
incorporated by reference herein, having the following formula. It
is prepared by spray-drying the following mixture:
______________________________________ Ingredient Parts by Weight
______________________________________ Sodium salt of ethoxylated
fatty alcohol 14.1 sulfate having an average of about 2.25 moles of
ethylene oxide per mole of fatty alcohol Sodium tallow alkyl
sulfate 2.4 Sodium silicate solids ratio: SiO.sub.2 /Na.sub.2 O =
2.0 6.0 Sodium tripolyphosphate
24.0 Na.sub.12 (AlO.sub.2.SiO.sub.2).27H.sub.2 O 18.0 Moisture 10.0
Sodium sulfate 25.0 Perfume substance of Table I of Example III 4.0
______________________________________
Laundry solutions containing the above detergent compositions are
used to launder fabrics. Each of the laundry compositions, both
prior to and on laundering, give rise to a pleasant aroma as set
forth in Table I of Example III.
EXAMPLE IX
PERFUMED LIQUID DETERGENT
Concentrated liquid detergents are prepared with aromas as set
forth in Table I of Example III containing 0.10%, 0.15% and 0.20%
of each of the substances of Table I of Example III in the liquid
detergent. The liquid detergent is a builder-free liquid detergent
consisting of (a) 50% of a nonionic surfactant having an HLB of 8.0
and a critical micelle concentration of 0.007 weight percent at
25.degree. C.; and (b) an anionic surfactant which is a
triethanolamine prepared according to United Kingdom Patent No.
1,491,603, the specification for which is incorporated by reference
herein.
The detergents all possess aromas as set forth in Table I of
Example III, supra.
EXAMPLE X
PREPARATION OF A DETERGENT COMPOSITION
A total of 100 grams of detergent powder (a low phosphate content
detergent composition which contains 12% by weight phosphate
builder, 8% hardness mineral ion insensitive detergent, 0.9% by
weight maleic anhydride-vinyl compound copolymer and 2% alkylene
oxide condensation product prepared according to Example IV at
column 9 of U.S. Pat. No. 4,000,080 issued on Dec. 28, 1976, the
specification for which is incorporated by reference herein) is
intimately admixed with 0.15 grams of one of the perfume materials
of Table I of Example III, supra, until a substantially homogeneous
composition is obtained. The composition has an aroma as set forth
in Table I of Example III, supra.
EXAMPLE XI
Each of the fragranced materials of Table I of Example III, supra,
are added to a 50:50 weight:weight mixture of low density
polyethylene:polyepsilon caprolactone PCL-700 forming pellets with
scents as set forth in Table I of Example III, supra.
75 Pounds of a mixture of PCL-700 polyepsilon caprolactone
(manufactured by the Union Carbide Corporation of New York, N.Y.,
having a melting point of about 180-190.degree. F.):low density
polyethylene are heated to about 250.degree. C. in a container of
the kind illustrated in FIGS. 2 and 3. 25 Pounds of each of the
fragrance materials as set forth in Table I of Example III are then
quickly added to the liqufied polymer mixture, the lid 228 is put
in place and the agitating means 273 are actuated. The temperature
is then raised to about 260.degree. F., and the mixing is continued
for 5-15 minutes. The valve V is then opened to allow flow of the
molten polymer enriched with perfume ingredient to exit through the
orifices 234. The liquid falling through the orifices 234
solidifies almost instanteously upon impact with the moving cooled
conveyor 238. Polymer beads or pellets 244 have pronounced scents
as described in Table I of Example III, supra, are thus formed.
Analysis demonstrates that the pellets contain about 25% of the
perfume material so that almost no losses in the scenting substance
did occur. These pellets may be called "master pellets."
50 Pounds of each batch of the scent containing "master pellets"
are then added to 1,000 pounds of unscented polypropylene, and the
mass is heated to the liquid state. The liquid is molded into thin
sheets of films. The thin sheets of films have pronounced aromas as
set forth in Table I of Example III, supra. The sheets of films are
cut into strips of 0.25 inches in width.times.3 inches in length
and placed into room air fresheners.
On operation of the room air freshener, after 4 minutes, the room
in each case has an aesthetically pleasing aroma with no foul odor
being present, the aroma being described in Table I of Example III,
supra.
* * * * *